Confidence Boost
by idekwthimdoin
Summary: (WINCEST) Everybody knows Dean is attractive. Sam needs a little reminder now and then from Dean that he's gorgeous too. It's really not Dean's fault that he falls for Sam.


**A/N HI THERE! I'm back with another story for you :) ENJOY**

 **WARNINGS: This contains some swearing, self esteem issues and a steamy scene or two, but no smut.**

1997

"Please don't talk to her, Dean." Sam was tugging on his brother's shirt to stop him from approaching Isabella Sanchez, A.K.A. the girl Sam has had a huge crush on ever since he enrolled in Valley View High.

"What? You asked me for help, and I'm helping you." Dean huffed. "I'm gonna say hi, then introduce you, jeez." Sam bit his lip nervously, his grip on Dean's shirt not loosening one bit.

"Just-just tell me what to do. If you go over there, She might…" Sam stopped mid-sentence. Dean wondered where all this insecurity was coming from. Sam had always been the shy one, but Dean found it ironic how his brother could shoot salt rounds at ghosts and how to recite exorcisms in Latin but he couldn't approach a girl without clamming up.

"She might what, Sam?" Dean crossed his arms, eyes narrowing. Sam bit his lip, remaining silent.

"Well if you don't need my help I'll just-" Sam tugged his brother even closer.

"Becauseshemightlikeyoubetter." Sam said hurriedly, his words cominh out all mushed together. Dean stared at him, awaiting some form of clarification. Sam sighed, before repeating what he said.

"She might like you better." Sam winced at how petulant he sounded.

"Why the hell would she like me better?" Dean furrowed his eyebrows in confusion.

"Because you're that," Sam gestured to Dean. "and I'm _this_." Sam gestured to himself, and Dean's heart clenched at the amount of disgust in Sam's tone. He lowered himself to look Sam in the eye.

"Hey, none of that self-loathing crap right now. You're gonna go over there, and knock her socks off with your amazing personality and wicked smarts, okay?" Dean said. Sam nodded slowly, uncertainty still evident.

"Back straight, and chin up." Sam followed his brother's instructions. "Now show me that smile of yours." Dean grunted as Sam shoved him playfully, letting out a small bubble of laughter.

"Attaboy. Now go introduce yourself." Dean gently pushed Sam towards Isabella, giving him an encouraging nod.

Sam went on his very first date a week later.

1998

Dean watched Sam watching girls in the park until he couldn't take it anymore. It was the middle of the summer, and they were drinking Slurpees on the park bench and Dean was restless.

"Dude, what the hell is wrong with you?" He asked Sam, who had no idea what crawled up Dean's ass.

"Go ask one of them out or something. Just watching you is killing me. Do you need a pep talk or something?" Dean asked, half joking.

"If it bothers you so much you why don't you go talk to them." Sam said calmly, taking another sip of his drink.

"Not interested in any of them." Dean looked around, until he saw a tall brunette with brown eyes half hidden by her hair. "Hey that one's cute."

"Go get her, then." Sam replied disinterestedly, not looking at where Dean was pointing.

"She's more your age, I think." Dean said, before sighing and giving up. "Whatever man, have fun being no fun." Dean pouted until a thought occurred to him.

"Sammy, are you gay?" Den couldn't help but grin as Sam started coughing and spluttering.

"Dude, no! What the hell?" Sam's voice rose 2 octaves higher.

"Just checking, Sammy. No need to get all worked up." Dean teased. Sam was about to reply when another walked pass and caught Sam's eye. She was tan and blonde and she winked at Sam as she passed. Sam blushed and ducked his head, hair falling into his eyes. Dean's breath hitched at the sight, probably since he'd finally figured out Sam's type.

So it was blondes then. Cool.

Dean nudged Sam to get his attention, then nodded at the blonde who was walking further and further away. Sam shook his head.

"She's not gonna go for scrawny and awkward, not if you're around." He grumbled.

"She winked at _you,_ dumbass. Some chicks actually dig the whole shy, awkward thing you got going on. They say it's cute, actually. Just give her the puppy dog thing, and you're good to go."

Sam sighed and opened his mouth to protest, then closed his mouth and reconsidered. A determined look crossed his face, and he stood up before brushing the dirt off his shorts. Sam turned to chase after the blonde after shooting one last look at his brother. Dean tried not to feel too lonely after.

1999

"What's got you all happy and dopey?" Dean asked as his brother _waltzed_ into their current apartment. Sam was grinning so wide from ear to ear, it made Dean want to smile too.

"I tutored Cindy Matthews at the library today." Sam was bouncing on the balls of his feet as he stripped off his hoodie. Dean rolled his eyes in fond exasperation. Only Sam could get excited over a freaking study section with a cute girl. It was quite endearing, really, but Dean would never admit that.

"You tutored her? You're a bigger nerd than I thought if you're all excited about getting to tutor a girl." Dean teased.

"We didn't study." Sam was smirking now, the little shit. Dean was about to inquire further when Sam pulled down the collar of his shirt, revealing a deep purple mark on his collarbone.

"That's my boy, Sammy! I was beginning to think we weren't related." Dean clapped his brother on the back, his hand moving up to squeeze the back of his neck. He ignored the dark feeling attempting to take over his chest. His brother was finally getting some action! He should be proud, not…whatever this feeling was.

"She was probably just trying to get out of having to study." Sam chuckled as he flopped down onto his bed. "Making out is definitely more fun than algebra. She might just have been bored out of her mind."

"Aww c'mon Sammy, don't be like that. I'm sure she was attracted to you, I mean you're…" Dean trailed off, not knowing what to say. Guys didn't usually compliment each other on looks, and definitely not brothers. Sam raised an eyebrow both in question and as a challenge.

Dean stared at his brother on the bed, where the late afternoon sun filtered through the blinds, forming a striped pattern on his Sam's body. A ray of light fell across Sam's face, making his eyes look golden and his cheekbones stand out. His long hair that Dean claimed to hate framed his face perfectly, making him look almost feminine. Sam's lips were redder than usual, and Dean was struck with the sudden and unexpected urge to kiss every single mole on Sam's face.

"Well?" Sam asked, breaking his brother's trance. Dean coughed awkwardly. He did _not_ want to kiss Sam. That would be weird.

"You're…not ugly." Dean winced internally. Was that the best he could come up with?

"Whatever, dude. I've made peace with the fact that I'm not hot and male model-y like y'know, _you_." Sam laughed, and if Dean had been paying attention he would have noticed that it sounded nervous.

Dean didn't notice because he was too busy tamping out the weird fluttery feeling in his stomach at Sam's description of him. He knew he was attractive, but Sam's affirmation made him feel all tingly.

"No seriously. You're a good-looking kid. If I were a girl I'd be all over you." Dean amended. Sam blushed and a small smile appeared on his face, which he tried to hide. Dean thought it was the most adorable thing ever. He grabbed the pillow nearest to him and chucked it at Sam's head.

"Such a freaking girl, Sam. Do you need me to constantly remind you that you're beautiful just the way you are?" Dean teased Sam to mask his nervousness. He never got nervous, and especially not around Sam. What the hell was happening to him?

"Screw you, asshole." Sam retorted, throwing a pillow into Dean's face. Soon it escalated into a full-blown pillow fight, and the boys' laughter could be heard through the motel walls.

When they had exhausted all their energy, they collapsed side by side onto one of the beds. Sam's face was flushed and his chest was heaving. He closed his eyes and tried to catch his breath, letting his smile linger on his face. Dean watched him the whole time, overwhelmed by how much he loved the boy lying next to him.

For the first time ever, Dean realized how _beautiful_ his brother was.

2000

Dean tried to enter the motel room as silently as he could, in case his brother was already asleep. Dean had been out of the bar, trying to get laid. He gave up when he couldn't stop looking for Sam in every girl he approached.

Sam was awake, however, and was seated at the dining table looking so miserable Dean felt bad for him. He looked up in surprise, as if he hadn't expected Dean to be back.

Sam's face was red and blotchy, and his eyes were shiny. Dean crossed the room in three strides, hurrying over in case his brother was hurt.

"Sam? Are you okay? Are you hurt?" Dean crouched in front of him, eyes roaming his brother's body as he checked for injuries. Tears just started rolling down Sam's cheeks though he bit his lips and shut his eyes in an attempt to stop them. The sight made Dean's heart ache.

"Hey, shush, it's okay. What's wrong Sammy? I can't help if I don't know what wrong." Dean gently ran his fingers through Sam's hair. It was a gesture that never failed to calm Sam down before, and it didn't fail him now. The tears stopped coming and Sam's breathing evened out into a more regular pattern. Sam was silent for a long time, but Dean waited patiently until his brother was ready to talk.

"What do they have that I don't?" Sam whispered so softly that Dean almost missed it.

"What are you talking about?" Dean asked.

"Those other girls that you love so much." Sam said, words bitter and clipped. "What do they have that I don't?"

Dean was stunned into silence. Dean didn't dare hope, but was it him or did Sam sound _jealous?_

"Sam I don't understand. A-Are you actually-"

"Jealous? Yes, I am. I'm jealous because you deserve better. They don't know you and you don't know them but you fuck them anyway. And I'm left sitting here wondering what I have to do to be good enough for you. And it sucks because I know I'll never be good enough because I'm a boy and I'm your brother and-"

"Sam." Dean shut his brother up with a single word, and they stared each other down. Well, it was more like Dean staring at Sam as he tried to keep eye contact but failing miserably as the tears reappeared. Dean would've laughed except that none of this was funny because his Sammy was hurting and Dean had been too blind to see.

"Sammy? Look at me." Dean waited for his brother to look at him instead of down at his shaking hands. "Do you want me? For real?"

"Yes." Sam's whispered confession hit Dean like a blow to the gut and he gasped before surging forward to press his mouth to Sam's. The kiss was rough and full of repressed feelings, as if he was making for all the times he held back when all he wanted to do was kiss Sam silly. When he pulled away, they were both gasping for air and Sam's face was red for an entirely different reason.

"Then I'm yours." Dean's lips ghosted down Sam's neck. "And you're mine." Dean said as he kissed Sam again, though it was nothing like the first. It was gentle and light and it was a good thing Sam was sitting because his knees turned to jelly.

"I've wanted this, for a long time." Dean figured there was no better time to admit it. Sam furrowed his brows in confusion.

"You wanted me? Why? How could you?"

"I looked for you in all those girls. But nothing ever came close to the real thing." Dean huffed when he saw the doubt in Sam's eyes. "You may not believe it Sammy, but you are _hot_. And I can't wait to get my hands all over you."

Sam's eyes darkened with lust and he grinned widely before standing and pushing Dean towards the bed. The rest of the night was spent with their hands all over each other, exploring places both familiar and new.

2012

Dean caught Sam looking at himself in the mirror, disgust clear in his eyes. Dean was about to tell him to hurry the hell up and go to bed so they could sleep until he realized what his brother was staring at. Sam's fingers traced over the scars over his body. Unlike Dean, when Sam had come back from hell, his body was exactly the same, and all his scars remained,

"You okay there, Sammy?" Dean asked.

"I look gross. Look at this shit." Sam pointed to his side, where a kitsune had once raked her claws down his ribs. It had been a deep wound, almost impossible to stitch. It happened while Dean was still in Hell, so he hadn't been there to help. He felt a spike of guilt in his chest.

Dean watched Sam scrutinize his scars until he decided enough was enough,

"Sam, come here." Dean called to him from the bed, _their_ bed. Since John died they didn't bother with the pretense of getting two beds, instead opting for a queen. Sam looked at him in confusion but did as he was told anyway. Dean pulled him down onto the bed, straddling him in one quick move.

"Dean, what are you-" Dean silenced Sam with a quick peck on the lips.

"I love you, you know that?" Dean only ever said those words to Sam, and every time he did, it never failed to make Sam blush and his heart race. Dean didn't give Sam a chance to reply as he moved to kiss his brother on the cheek, where the daevas from years ago had scratched him.

"And I love this." A kiss on Sam's temple where Gordon had punched him so hard his skin split. Dean was glad the bastard was dead.

"And this" A kiss on Sam's collar bone where it was slightly dented from when a poltergeist threw him into a table and broke the collarbone. Dean made sure to leave a mark there.

"This too" A scar from when a bullet grazed his brother as they tried to escape from the police.

Dean worked his way downwards, leaving his own little marks as he progressed. He savored every noise that came from his brother, grinning when he saw Sam's sweats begin to tent.

"Dean, please." Sam whimpered.

"Don't worry Sammy I'll take care of you. But tell me something;" Dean moved back up to whisper into Sam's ear. "Do you still feel ugly?"

Sam shivered, shaking his head. Dean had a way of making him feel wanted and Sam thanked whoever was listening that he had someone like Dean in his life.

It definitely wasn't the last time Sam felt insecure about himself, but it was okay because Dean was always around to knock some sense into him.

 **A/N Sooo i hope you liked it, and if you did please leave a fav and/or review. Constructive criticism is welcome!**


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